EP0408947A2 - Article en résine de mélamine à élasticité accrue - Google Patents

Article en résine de mélamine à élasticité accrue Download PDF

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Publication number
EP0408947A2
EP0408947A2 EP90112405A EP90112405A EP0408947A2 EP 0408947 A2 EP0408947 A2 EP 0408947A2 EP 90112405 A EP90112405 A EP 90112405A EP 90112405 A EP90112405 A EP 90112405A EP 0408947 A2 EP0408947 A2 EP 0408947A2
Authority
EP
European Patent Office
Prior art keywords
melamine
hydroxy
substituted
mol
formaldehyde
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP90112405A
Other languages
German (de)
English (en)
Other versions
EP0408947A3 (en
EP0408947B1 (fr
Inventor
Jürgen Dr. Weiser
Wolfgang Dr. Reuther
Gerhard Dr. Turznik
Wolfgang Dr. Fath
Heinz Berbner
Onno Dr. Graalmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0408947A2 publication Critical patent/EP0408947A2/fr
Publication of EP0408947A3 publication Critical patent/EP0408947A3/de
Application granted granted Critical
Publication of EP0408947B1 publication Critical patent/EP0408947B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141Hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32Melamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40Chemically modified polycondensates
    • C08G12/42Chemically modified polycondensates by etherifying
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/94Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of other polycondensation products
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2361/00Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
    • C08J2361/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08J2361/26Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08J2361/28Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine

Definitions

  • the invention relates to moldings, in particular foams and fibers made of melamine / formaldehyde condensation resins with increased elasticity, in which part of the melamine is replaced by substituted melamine.
  • Foams and fibers from melamine resins are known, e.g. B. from DE-A-29 15 457 and DE-A-23 64 091.
  • the present invention was based on the object of improving the elasticity of such moldings.
  • DE-A-29 15 457 describes foams made from melamine / formaldehyde condensation resins in which melamine can be replaced in whole or in part by alkyl-substituted melamine. A replacement by hydroxyoxaalkyl melamine is not disclosed.
  • EP-A 221 330 describes moldings, preferably foams and fibers made of melamine-formaldehyde condensation resins, in which 1 to 80% by weight of the melamine is replaced by hydroxyalkylamine-melamine. The addition increases the strength, but reduces the elasticity.
  • the melamine-formaldehyde condensation product suitable for the production of the moldings are known and are described, for example, in DE-A-29 15 457.
  • the molar ratio of melamine to formaldehyde can vary within wide limits between 1: 1.5 to 1: 4.5, preferably it is between 1: 2.5 and 1: 3.5.
  • Hydroxyoxaalkylmelamines - in contrast to hydroxyethylmelamines - can be stored indefinitely in aqueous solution. According to the invention, 0.1 to 70 mol% of the melamine is replaced by hydroxy-oxaalkyl-melamine in the known melamine-formaldehyde condensation production.
  • 1 to 70, preferably 2 to 50 and in particular 5 to 25 mol% of the substituted melamine are expediently used.
  • melamine and substituted melamine are polycondensed together with formaldehyde.
  • the resins generally have a molar ratio of the melamine components to formaldehyde of 1: 1.5 to 1: 4.5, preferably 1: 2.5 to 1: 3.5.
  • They can contain small amounts of conventional additives, such as disulfite, formide, citrate, phosphate, polyphosphate, urea, dicyandiamide or cyanamide.
  • the molded articles are produced by curing the resins in a customary manner by adding small amounts of acids, preferably formic acid.
  • Foams can be produced by foaming an aqueous solution or dispersion which contains the melamine / formaldehyde precondensate modified according to the invention, an emulsifier, a blowing agent and a hardener, and, if appropriate, conventional additives, and then curing the foam. It has been shown that particularly Elastic foams are obtained if relatively high-concentration, preferably over 68 percent by weight and in particular over 72 percent by weight solutions or dispersions are used (the concentrations refer to the mixture of resin and water without additives) and if one foams under such conditions that initially only there is a slight increase in viscosity and the hardening process, with a sharp increase in viscosity, only begins when the foaming process has largely ended. Such a method is described in detail in DE-A-29 15 457. The foams obtained are characterized by increased elasticity, elongation at break and tensile strength.
  • the melamine-formaldehyde resin modified according to the invention is spun in a manner known per se after the addition of a hardener in a heated atmosphere and, at the same time, the solvent (H2O) is evaporated and the condensate is cured.
  • a hardener in a heated atmosphere
  • the solvent H2O
  • the condensate is cured.
  • Such a method is described in detail in DE-A-23 64 091.
  • the fibers obtained are characterized by increased elongation and low sliding friction.
  • the elongation at break of the HOM fibers is 30% (cf. HEM 15%).
  • a coefficient of 0.65 was determined at a speed of 2 mm / s (HEM 0.9).
  • the foamable mixture obtained in this way is foamed and cured at 120 degrees in a microwave oven while irradiating microwave energy.
  • the raw foam is then flowed through with air at 250 degrees for 30 minutes.
  • the finished foam has a density of 12 kg / m3. 17% of the melamine is replaced by hydroxy-oxapentyl melamine.
  • the elongation at break (DIN 53 455) is increased by 25%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Textile Engineering (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Artificial Filaments (AREA)
EP90112405A 1989-07-11 1990-06-29 Article en résine de mélamine à élasticité accrue Expired - Lifetime EP0408947B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3922733A DE3922733A1 (de) 1989-07-11 1989-07-11 Formkoerper aus melaminharzen mit erhoehter elastizitaet
DE3922733 1989-07-11

Publications (3)

Publication Number Publication Date
EP0408947A2 true EP0408947A2 (fr) 1991-01-23
EP0408947A3 EP0408947A3 (en) 1991-07-31
EP0408947B1 EP0408947B1 (fr) 1994-03-09

Family

ID=6384709

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90112405A Expired - Lifetime EP0408947B1 (fr) 1989-07-11 1990-06-29 Article en résine de mélamine à élasticité accrue

Country Status (4)

Country Link
US (1) US5084488A (fr)
EP (1) EP0408947B1 (fr)
JP (1) JP3219272B2 (fr)
DE (2) DE3922733A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5322915A (en) * 1991-07-12 1994-06-21 Basf Aktiengesellschaft Modified melamine-formaldehyde resins
EP0602516A1 (fr) * 1992-12-14 1994-06-22 BASF Aktiengesellschaft Procédé pour la destruction chimique des résines aminoplastes durcis
EP0643085A1 (fr) * 1993-09-11 1995-03-15 BASF Aktiengesellschaft Résines mélamine-formaldéhyde insolubles dans l'eau
EP0648756A1 (fr) * 1993-09-15 1995-04-19 BASF Aktiengesellschaft Procédé de préparation de hydroxyalkyl mélamines
WO1996020229A1 (fr) * 1994-12-23 1996-07-04 Basf Aktiengesellschaft Procede de preparation de produits de condensation de melamine-formaldehyde colores
EP0764669A1 (fr) * 1995-09-22 1997-03-26 Basf Aktiengesellschaft Résines de mélamine élastifiées
US5624466A (en) * 1994-09-15 1997-04-29 Basf Aktiengesellschaft Dyeing of melamine-formaldehyde condensation products
WO1997031958A1 (fr) * 1996-03-01 1997-09-04 Basf Aktiengesellschaft Produits de condensation a base de triazines et de formaldehyde
US5916999A (en) * 1996-04-22 1999-06-29 Basf Aktiengesellschaft Process for producing filaments from melamine/formaldehyde condensation products
US6004892A (en) * 1994-11-12 1999-12-21 Basf Aktiengesellschaft Fire protection covers made of melamine-formaldehyde resin fibers
US7012108B2 (en) 2000-12-15 2006-03-14 Agrolinz Melamin Gmbh Modified inorganic particles
US7196131B2 (en) 2000-12-15 2007-03-27 Agrolinz Melamin Gmbh Polymer-modified inorganic particles
US7208540B2 (en) 2000-12-15 2007-04-24 Agrolinz Melamin Gmbh Process for curing aminoplast resins
US8163664B2 (en) 2004-07-30 2012-04-24 Owens Corning Intellectual Capital, Llc Fiberglass products for reducing the flammability of mattresses
US8722779B2 (en) 2007-10-12 2014-05-13 Borealis Agrolinz Melamine Gmbh Thermoplastically processible aminoplastic resin, thermoset microfibre non-wovens, and process and plant for their production

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4315609A1 (de) * 1993-05-11 1994-11-17 Basf Ag Verfahren und Vorrichtung zur Herstellung von Fasern nach einem Zentrifugalspinnverfahren
US5496625A (en) * 1994-12-30 1996-03-05 Norfab Corporation Melamine thermal protective fabric and core-spun heat resistant yarn for making the same
DE19617634A1 (de) 1996-05-02 1997-11-06 Basf Ag Flammfeste Gewebe auf der Basis von Melamin-Harzfasern
DE19735809A1 (de) * 1997-08-18 1999-02-25 Basf Ag Kontinuierliches Verfahren zur Herstellung von Amino- und/oder Phenoplasten
US6200355B1 (en) 1999-12-21 2001-03-13 Basf Corporation Methods for deep shade dyeing of textile articles containing melamine fibers
DE10056398B4 (de) * 2000-11-14 2006-12-14 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Aus der Schmelze verarbeitbares Aminoharz auf Basis von 1,3,5-Triazinen und Aldehyden
DE10133787A1 (de) * 2001-07-16 2003-02-06 Basf Ag Flammfeste textile Flächengebilde
EP1448671B1 (fr) 2001-11-19 2007-09-12 AMI Agrolinz Melamine International GmbH Produits, en particulier matieres a mouler, a savoir des polymeres contenant des segments triazine, leur procede de production et leurs utilisations
US7629043B2 (en) 2003-12-22 2009-12-08 Kimberly-Clark Worldwide, Inc. Multi purpose cleaning product including a foam and a web
US20060068675A1 (en) * 2004-09-01 2006-03-30 Handermann Alan C Wet-lay flame barrier
US7589037B2 (en) * 2005-01-13 2009-09-15 Basofil Fibers, Llc Slickened or siliconized flame resistant fiber blends
US20060229229A1 (en) * 2005-04-11 2006-10-12 Kimberly-Clark Worldwide, Inc. Cleaning composite
DE102005027040A1 (de) * 2005-06-10 2006-12-14 Basf Ag Flächengebilde und Formkörper zur Reinigung von Oberflächen
US20070166488A1 (en) * 2006-01-19 2007-07-19 Trefethren Susan M Cleaning composite comprising lines of frangibility
JP2009534070A (ja) * 2006-04-18 2009-09-24 ビーエーエスエフ ソシエタス・ヨーロピア 殺菌可能な原料としてのアミノプラストに基づいた発泡材料
JP4888330B2 (ja) * 2007-10-22 2012-02-29 トヨタ自動車株式会社 直接噴射式の内燃機関
EP2703074A1 (fr) * 2012-09-04 2014-03-05 Basf Se Procédé de fabrication de mousses à base de mélamine/formaldéhyde
EP3085817A4 (fr) * 2013-12-20 2017-08-02 Nissan Chemical Industries, Ltd. Fibres, composition permettant de produire des fibres, et biomatériau contenant les fibres
JP7086957B6 (ja) 2016-11-23 2022-07-04 ビーエーエスエフ ソシエタス・ヨーロピア メラミン-ホルムアルデヒド発泡体を製造する方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3531912A1 (de) * 1985-09-07 1987-03-19 Basf Ag Hydroxyoxaalkylmelamine, verfahren zu ihrer herstellung und deren verwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2915457A1 (de) * 1979-04-17 1980-10-30 Basf Ag Elastischer schaumstoff auf basis eines melamin/formaldehyd-kondensationsproduktes
DE3534740A1 (de) * 1985-09-28 1987-04-09 Basf Ag Formkoerper aus melaminharzen mit erhoehter festigkeit

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3531912A1 (de) * 1985-09-07 1987-03-19 Basf Ag Hydroxyoxaalkylmelamine, verfahren zu ihrer herstellung und deren verwendung

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5322915A (en) * 1991-07-12 1994-06-21 Basf Aktiengesellschaft Modified melamine-formaldehyde resins
EP0602516A1 (fr) * 1992-12-14 1994-06-22 BASF Aktiengesellschaft Procédé pour la destruction chimique des résines aminoplastes durcis
US5530031A (en) * 1993-09-11 1996-06-25 Basf Aktiengesellschaft Water-insoluble melamine-formaldehyde resins
EP0643085A1 (fr) * 1993-09-11 1995-03-15 BASF Aktiengesellschaft Résines mélamine-formaldéhyde insolubles dans l'eau
US5637704A (en) * 1993-09-15 1997-06-10 Basf Aktiengesellschaft Preparation of hydroxyoxaalkylmelamines
EP0648756A1 (fr) * 1993-09-15 1995-04-19 BASF Aktiengesellschaft Procédé de préparation de hydroxyalkyl mélamines
US5624466A (en) * 1994-09-15 1997-04-29 Basf Aktiengesellschaft Dyeing of melamine-formaldehyde condensation products
US6004892A (en) * 1994-11-12 1999-12-21 Basf Aktiengesellschaft Fire protection covers made of melamine-formaldehyde resin fibers
CN1072235C (zh) * 1994-12-23 2001-10-03 巴斯福股份公司 制备着色三聚氰胺-甲醛缩聚物的方法
US5837013A (en) * 1994-12-23 1998-11-17 Basf Aktiengesellschaft Preparation of colored melamine-formaldehyde condensation products
WO1996020229A1 (fr) * 1994-12-23 1996-07-04 Basf Aktiengesellschaft Procede de preparation de produits de condensation de melamine-formaldehyde colores
EP0764669A1 (fr) * 1995-09-22 1997-03-26 Basf Aktiengesellschaft Résines de mélamine élastifiées
WO1997031958A1 (fr) * 1996-03-01 1997-09-04 Basf Aktiengesellschaft Produits de condensation a base de triazines et de formaldehyde
US5916999A (en) * 1996-04-22 1999-06-29 Basf Aktiengesellschaft Process for producing filaments from melamine/formaldehyde condensation products
US7012108B2 (en) 2000-12-15 2006-03-14 Agrolinz Melamin Gmbh Modified inorganic particles
US7196131B2 (en) 2000-12-15 2007-03-27 Agrolinz Melamin Gmbh Polymer-modified inorganic particles
US7208540B2 (en) 2000-12-15 2007-04-24 Agrolinz Melamin Gmbh Process for curing aminoplast resins
US8163664B2 (en) 2004-07-30 2012-04-24 Owens Corning Intellectual Capital, Llc Fiberglass products for reducing the flammability of mattresses
US8722779B2 (en) 2007-10-12 2014-05-13 Borealis Agrolinz Melamine Gmbh Thermoplastically processible aminoplastic resin, thermoset microfibre non-wovens, and process and plant for their production

Also Published As

Publication number Publication date
JP3219272B2 (ja) 2001-10-15
DE3922733A1 (de) 1991-01-24
EP0408947A3 (en) 1991-07-31
DE59004871D1 (de) 1994-04-14
US5084488A (en) 1992-01-28
JPH03231957A (ja) 1991-10-15
EP0408947B1 (fr) 1994-03-09

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